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Cis and trans 4,8‐dimethyl‐6‐phenyl‐5,6,7,8‐tetra‐hydro‐4 H ‐1,3,6‐oxadiazocin‐2‐ones: Conformational studies and configurational assignments by NMR
Author(s) -
Nishiyama Tomihiro,
Fujiwara Toyokuni,
Miyazaki Satoshi,
Yamada Fukiko
Publication year - 1992
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570290626
Subject(s) - chemistry , tetra , aniline , phosgene , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry
The reaction of N ‐(2‐aminopropyl)‐ N ‐(2‐hydroxypropyl)aniline with phosgene afforded cis and trans isomers of 4,8‐dimethyl‐6‐phenyl‐5,6,7,8‐tetrahydro‐4 H ‐1,3,6‐oxadiazocin‐2‐one. On the basis of ASIS data and Eu‐shift difference, the title compounds are found to exist as boat‐chair conformation in which the carbonyl carbon resides at the BC‐2 position on the molecular plane.